Working It

I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago. Several professional painters came in and they all wanted $700 or more to do the job. I decided to ask my friends if they knew someone who might do it for less.

One of my friends told me about Jim, a young guy going to college, who also has a painting business on the side. She told me that he immediately came to mind, because being best friends with his sister, she knew he was also a crossdresser. I suggested she give him my phone number and website and ask him to call if he was interested in a possible barter. Less than an hour later the phone rang. The conversation went something like this:

“Hi, Miss Bowers?” “This is she” “This is Jim from Paragon Painting, Susan told me you need some work done” “I do indeed Jim. Would you like to come over and discuss it?” “Sure, by the way I love your website. I don’t know if she mentioned it but, uh, I, uh, maybe we can work something out” “Absolutely, I’m sure we could. When can you come over to take a look?” “How about tonight around 7:00?” “Perfect, see ya then”

I discussed it with my girlfriend and made sure she was there to help me decide if this was a good idea. 7:00 sharp his van pulled up.

“Wow-he’s cute isn’t he? And besides a having a recommendation, we know his address and everything! This will be fun”

“Lets meet him first OK? You’re too trusting sometimes Teresa”.

“That’s why you’re here Ashley. I’ll let him in”

Hi, Miss Bowers? I’m Jim”

“Come in Jim, and you can call me Teresa. I want you to meet my friend Ashley”

“No don’t. I want to know all about you! I was hoping we could work out some kind of arrangement rather than cash for the job. Let me show you the room and then we’ll talk. Its right here. I need that hole patched, then the ceiling painted. And since the whole room will be covered, I thought we might as well paint the whole thing”.

“I’ll do it!”

“You’ll do what?”

“I’ll do the job for you, let me go get you some color charts”

“But we haven’t talked about the price? Sit down on the bed and tell me about yourself”

“Well, I’m going to school for art, and”

“Not that stuff silly, Do you like to wear girls clothes Jim?”

“Uh, can you get me some water or something please?”

“Sure, go get those charts and we’ll go over all the details”

“So, will he paint the ceiling?”

“I have a feeling I can get him to paint the whole house, but I don’t feel like moving everything. I want to do it, what do you think?”

“He does seem harmless. What does he want exactly?”

“I’ll let you know, probably just the usual dressing up and help with his makeup. Its got to be worth it to get all that finally finished right? Here he comes, you look over the color charts while we talk.

Give that stuff to Ashley, I want to ask you a few more questions in private, OK? Walk this way”

“I wish I could walk that way!”

“That’s what we’re going to talk about. Here’s your water, just relax and be honest with me. How long have you been dressing up as a girl?”

“OK Teresa, I’ve never really told anyone about this but I want to. I think I can trust you. I’ve been dressing up since I was about 7 or 8. I used to wear my sisters clothes all the time. I just loved it for some reason. It was all I could think about!

As I got older I started wearing my Mom’s stuff too. Everything! I knew it was crazy but I just couldn’t stop! Panties, bras, nightgowns, stockings, skirts, blouses, dresses, even her heels! They never actually caught me but I’m sure they knew. As I got older, I started fantasizing about having someone dress me up. Usually against my will! Is that crazy or what?”

“Darling, you’ve been to my website, and heard my stories right? I have heard this before you know. Please, go on”

“I want to be dressed up completely! I want to shave all my body hair, be put into silky lingerie, have my hair done, full makeup, my nails painted, be forced to wear stockings and a garter belt and heels. Then, I want to be teased, and made to talk and walk like a girl. Maybe in front of your friends! Then I want pictures taken of me in all kinds of sexy poses! In different outfits! I’ve been dreaming about this my whole life Teresa, I want it so badly but I’m afraid of actually doing it!”

“Two coats on the ceiling and walls?”

“What, do you mean, you’ll do it? All of that, even the pictures?”

“I’ll even put them on a CD for you to take home. When can you start?”

“Oh my God-I-now! Tomorrow! Whenever you want! Oh my God!

“Easy now girl, finish your water. We’ll call you with a color, and you can start Monday. Finish the job, help me put everything back, and I’ll spend the next day making you into Jamie. How does that sound?”

“Like Heaven Teresa-just like Heaven!”

“Run along now Jamie and we’ll see you around 9:00, is that good for you?’

“Oh my God! Whenever you want! Oh my God!

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